Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines

被引：38

作者：

Adib, Mehdi ^{[1
]}

Mohamadi, Ali ^{[1
]}

Sheikhi, Ehsan ^{[1
]}

Ansari, Samira ^{[1
]}

Bijanzadeh, Hamid Reza ^{[2
]}

机构：

[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran

[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

SYNLETT | 2010年 / 11期

关键词：

imidazo[1,2-a]pyridines; pyridines; alpha-bromoketones; ammonium acetate; microwave irradiation; solvent-free synthesis; cyclizations; heterocycles; 3-COMPONENT SYNTHESIS; IRRADIATION; DERIVATIVES; ANTAGONISTS; INHIBITOR; APOPTOSIS; ACCESS; SALTS;

D O I：

10.1055/s-0029-1219962

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient synthesis of imidazo[1,2-a]pyridines is described. N-Phenacylpyridinium bromides, which were prepared in situ from the addition of pyridines to alpha-bromoketones, undergo nucleophilic addition of ammonium acetate under microwave irradiation and solvent-free conditions to afford the corresponding imidazo[1,2-a]pyridines in excellent yields.

引用

页码：1606 / 1608

页数：3

共 38 条

[1] A new, one-pot, multi-component synthesis of imines of 3-amino-2-arylimidazo[1,2-a]pyridines, 3-amino-2-arylimidazo[1,2-a]pyrazines, and 3-amino-2-arylimidazo[1,2-a]pyrimidines
Abid, Mehdi
Sheibani, Esmail
Bijanzadeh, Hamid Reza
Zhu, Long-Guan
[J]. TETRAHEDRON, 2008, 64 (47) : 10681 - 10686
[2] Efficient highly diastereoselective synthesis of 1,8a-dihydro-7H-imidazo[2,1-b][1,3]oxazines
Adib, M
Sheibani, E
Mostofi, M
Ghanbary, K
Bijanzadeh, HR
[J]. TETRAHEDRON, 2006, 62 (14) : 3435 - 3438
[3] A Novel, One-Pot, Efficient Synthesis of 2-Aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones
Adib, Mehdi
Sayahi, Mohammad Hosein
Ziyadi, Hakimeh
Zhu, Long-Guan
Bijanzadeh, Hamid Reza
[J]. SYNTHESIS-STUTTGART, 2008, 20 (20): : 3289 - 3294
[4] An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines
Adib, Mehdi
Sheibani, Esmail
Zhu, Long-Guan
Mirzaei, Peiman
[J]. TETRAHEDRON LETTERS, 2008, 49 (34) : 5108 - 5110
[5] A novel and simple synthesis of 9H-Pyrimido[4,5-b]indoles under microwave irradiation and solvent-free conditions
Adib, Mehdi
Mohammadi, Bagher
Bijanzadeh, Hamid Reza
[J]. SYNLETT, 2008, (02) : 177 - 180
[6] A new, one-pot, three-component synthesis of 4H-pyrido[1,2-a]-pyrimidines, 4H-pyrimido[1,2-a]pyrimidines, and 4H-pyrazino[ 1,2-a] pyrimidines
Adib, Mehdi
Sayahi, Mohammad Hosein
Ziyadi, Hakimeh
Bijanzadeh, Hamid Reza
Zhu, Long-Guan
[J]. TETRAHEDRON, 2007, 63 (45) : 11135 - 11140
[7] Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water
Adib, Mehdi
Mahdavi, Mohammad
Noghani, Mahsa Alizadeh
Mirzaei, Peiman
[J]. TETRAHEDRON LETTERS, 2007, 48 (41) : 7263 - 7265
[8] One-pot three-component synthesis of 3-Amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines
Adib, Mehdi
Koloogani, Somayeh Aali
Abbasi, Alireza
Bijanzadeh, Hamid Reza
[J]. SYNTHESIS-STUTTGART, 2007, (19): : 3056 - 3060
[9] Efficient synthesis of imidazo[1,2-a]pyridin-3(2H)-ones
Adib, Mehdi
Mahdavi, Mohammad
Abbasi, Alireza
Jahromi, Amin Haghighat
Bijanzadeh, Hamid Reza
[J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3217 - 3220
[10] A novel, one-pot, three-component synthesis of 1,2,4-oxadiazoles under microwave irradiation and solvent-free conditions
Adib, Mehdi
Mahdavi, Mohammad
Mahmoodi, Niusha
Pirelahi, Hooshang
Bijanzadeh, Hamid Reza
[J]. SYNLETT, 2006, (11) : 1765 - 1767

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